Organosulfur compound, process for producing the same, and organic electroluminescence element using the same

Abstract

Disclosed is an organosulfur compound denoted by a general formula (a1): in which A denotes —S—, —S(O)— or —S(O) 2 —; Z 1 and Z 4 denote a trivalent aromatic hydrocarbon group or the like; Z 2 and Z 3 denote a bivalent aromatic hydrocarbon group or the like; Ar 1 , Ar 2 , Ar 3 and Ar 4 denote an aromatic hydrocarbon group or the like; and n is 0 or 1, or a general formula (b1): in which A denotes the same meaning as aforesaid; Z 5 denotes a trivalent aromatic hydrocarbon group or the like; Ar denotes a m-valent aromatic hydrocarbon group or the like; Ar 1 and Ar 2 denote the aforesaid meaning; and m is 2 or 3. This compound is useful as an electron transport material, a hole blocking material or a host material of an organic electroluminescence element.

The invention claimed is: 
     
       1. An organosulfur compound denoted by a general formula (a1): 
       
         
           
           
               
               
           
         
       
       in which,
 A denotes —S(O) 2 —, 
 Z 1  and Z 4  denote 
 
       
         
           
           
               
               
           
         
         
           Z 2  and Z 3  denote 1,4-phenylene, 
         
         Ar 1 , Ar 2 , Ar 3  and Ar 4  denote a phenyl group, tolyl group or pyridyl group, wherein Ar 1 , Ar 2 , Ar 3  and Ar 4  are all the same, and 
         n is 0 or 1, wherein two of n are the same, 
       
       or,
 a general formula (b1): 
 
       
         
           
           
               
               
           
         
       
       in which,
 A denotes —S(O) 2 —, 
 Z 5  denotes 
 
       
         
           
           
               
               
           
         
         Ar denotes a divalent residue derived from benzene, 
         Ar 1  and Ar 2  denote a phenyl group, tolyl group or pyridyl group, wherein Ar 1  and Ar 2  are the same, and, 
         m is 2. 
       
     
     
       2. An organosulfur compound according to  claim 1 , denoted by a general formula (a5), (a6), (b5) or (b6): 
       
         
           
           
               
               
           
         
         in which, Ar 11  denotes a phenyl group, tolyl group or pyridyl group, and 
       
       
         
           
           
               
               
           
         
         in which, Ar 1  and Ar 2  denote a phenyl group. 
       
     
     
       3. A process for producing a compound denoted by a general formula (a1): 
       
         
           
           
               
               
           
         
       
       in which,
 A denotes —S(O) 2 —, 
 Z 1  and Z 4  denote 
 
       
         
           
           
               
               
           
         
         Z 2  and Z 3  denote 1,4-phenylene, 
         Ar 1 , Ar 2 , Ar 3  and Ar 4  denote a phenyl group, tolyl group or pyridyl group, wherein Ar 1 , Ar 2 , Ar 3  and Ar 4  are all the same, and 
         n is 0 or 1, wherein two of n are the same; 
       
       wherein a compound denoted by a general formula (c1): 
       
         
           
           
               
               
           
         
       
       in which,
 A, Z 1 , Z 4 , Z 2 , Z 3  and n denote the meanings as defined for said general formula (a1), 
 X 1 , X 2 , X 3  and X 4  independently denote a halogen, 
 
       is reacted with a compound denoted by formulae:
   Ar 1 P, Ar 2 P, Ar 3 P and Ar 4 P 
 in which, Ar 1 , Ar 2 , Ar 3  and Ar 4  denote the meanings as defined for said general formula (a1); P is an eliminative group which is selected so that a compound comprising P is a boronic acid, a boronate ester, or an organometallic reagent. 
 
     
     
       4. A process for producing a compound denoted by a general formula (a1): 
       
         
           
           
               
               
           
         
       
       in which,
 A denotes —S(O) 2 —, 
 Z 1  and Z 4  denote 
 
       
         
           
           
               
               
           
         
         Z 2  and Z 3  denote 1,4-phenylene, 
         Ar 1 , Ar 2 , Ar 3  and Ar 4  denote a phenyl group, tolyl group or pyridyl group, wherein Ar 1 , Ar 2 , Ar 3  and Ar 4  are all are the same, and 
         n is 0 or 1, wherein two of n are the same; 
       
       wherein a compound denoted by a general formula (c4): 
       
         
           
           
               
               
           
         
       
       in which,
 A, Z 2 , Z 3  and n denote the meanings as defined for said general formula (a1), and 
 X denotes a halogen, and two of X may be the same or different, 
 
       is reacted with a compound denoted by general formulae (c5i) and (c5ii): 
       
         
           
           
               
               
           
         
       
       in which,
 Ar 1 , Ar 2 , Ar 3 , Ar 4 , Z 1  and Z 4  denote the meanings as defined in said general formula (a1), 
 P is an eliminative group which is selected so that a compound comprising P is a boronic acid, a boronate ester, or an organometallic reagent. 
 
     
     
       5. A process for producing a compound denoted by a general formula (b1): 
       
         
           
           
               
               
           
         
       
       in which,
 A denotes —S(O) 2 —, 
 Z 5  denotes 
 
       
         
           
           
               
               
           
         
         Ar denotes a divalent residue derived from benzene, 
         Ar 1  and Ar 2  denote a phenyl group, tolyl group or pyridyl group, wherein Ar 1  and Ar 2  are the same, and 
         m is 2, 
         wherein a compound denoted by a general formula (d1): 
       
       
         
           
           
               
               
           
         
       
       in which,
 A, Ar, Z 5  and m denote the meanings as defined for said general formulae (b1), 
 X 1  and X 2  independently denote a halogen, 
 
       is reacted with a compound denoted by formulae
   Ar 1 P and Ar 2 P 
 
       in which, Ar 1  and Ar 2  denote the meanings as defined in said general formula (b1); P is an eliminative group which is selected so that a compound comprising P is a boronic acid, a boronate ester, or an organometallic reagent. 
     
     
       6. An organic electroluminescence element comprising the organosulfur compound according to  claim 1 . 
     
     
       7. An organic electroluminescence element according to  claim 6 , wherein at least one layer selected from an electron transporting layer, a hole blocking layer and an emissive layer comprises the organosulfur compound according to  claim 1 . 
     
     
       8. An organic electroluminescence element according to  claim 7 , wherein the emissive layer comprises 4-acetylphenylethynyl[1,3-bis(2,6-diisopropylphenyl)imidazole-2-ylidene]gold.